In Germany, the entry into the labor market for students in the nonacademic tracks of secondary schools may take multiple pathways. Students graduating from lower track secondary schools (LTSS) face major problems in school-towork transitions, prompting the provision of intensive career guidance in school. In a case study for the City of Freiburg, this paper analyzes skill formation, career guidance, and the first transition after graduation for LTSS students in the late 2000s. We find that only about 10% of LTSS students start an apprenticeship immediately after graduation. Instead, about half of the LTSS students, typically those with better school grades, participate in additional general teaching (AGT) and rather enter further schooling than an apprenticeship. In addition, the majority of students with poor school grades continue with pre-vocational training. The latter group involves a large share of male students with a migration background. Our findings show a large heterogeneity among LTSS students, most visible in the division between students with and without AGT. Furthermore, characteristics observable at the end of grade 7 have a strong predictive power on the transition after graduation, and focusing career guidance on the immediate start of an apprenticeship after graduation may be misplaced.